Renewable bio-based (meth)acrylated monomers as vinyl ester cross-linkers
Anhydrosugar-based monomers prepared from isosorbide, isomannide, and isoidide and resin systems containing these anhydrosugar-based monomers that are partially to fully bio-based, which may produce materials having properties that meet or exceed the properties of similar petroleum derived vinyl ester resins.
1. A method of making a polymer comprising the step of curing a composition comprising at least one polymerizable monomer selected from the group consisting of:
2. The method of claim 1 , wherein the curing is carried out by free-radical curing.
3. The method of claim 1 , wherein the composition further comprises from 1 to 99% by weight of at least one reactive diluent selected from the group consisting of: styrene, 2-hydroxymethacrylate, methyl methacrylate, methyl acrylate, furfuryl methacrylate, methacrylated lauric acid, and methacrylated fatty acids.
4. The method of claim 1 , wherein the composition further comprises from 1 to 99% by weight of at least one cross-linking agent.
5. The method of claim 4 , wherein the crosslinker is selected from the group consisting of: unsaturated polyester, vinyl ester and the structures in claim 1 .
6. A polymer obtained by the process of claim 1 .
7. A method of making a polymer comprising the step of curing a composition comprising at least one vinyl ester resin monomer or unsaturated polyester monomer and at least one anhydrosugar-based polymerizable monomer selected from the group consisting of:
8. The method of claim 7 , wherein the composition comprises 1-99% by weight of anhydrosugar-based monomers, 1-70% by weight of vinyl ester resin monomer and/or unsaturated polyester monomer and 0-60% by weight of at least one reactive diluent.
9. The method of claim 7 wherein the composition comprises 5-95% by weight by weight of anhydrosugar-based monomers, 5-65% by weight of vinyl ester resin monomer and/or unsaturated polyester monomer and 0-50% by weight of at least one reactive diluent.
10. The method of claim 7 , wherein the composition comprises 15-90% by weight of anhydrosugar-based monomers, 10-55% by weight of vinyl ester resin monomer and/or unsaturated polyester monomer and 0-45% by weight of at least one reactive diluent.
11. The method of claim 8 , wherein the reactive diluent is selected from the group consisting of: styrene, 2-hydroxymethacrylate, methyl methacrylate, methyl acrylate, furfuryl methacrylate, methacrylated lauric acid and methacrylated fatty acids.
12. The method of claim 11 , wherein the vinyl ester monomer is selected from the group consisting of (meth)acrylated glycidyl ethers of bisphenols, (meth)acrylated ethoxylated bisphenols and novolac vinyl esters.
13. The method of claim 12 , wherein the bisphenols are selected from the group consisting of: bisphenol A, hexafluorobisphenol A, bisphenol E, bisphenol F, tetramethyl bisphenol E, tetramethyl bisphenol F, bisphenol M, bisphenol C, bisphenol P and bisphenol Z.
14. The method of claim 13 , wherein the unsaturated polyester monomer is made from one or more of the following components: phthalic acid, terephthalic acid, m-phthalic acid, suberic acid, adipic acid, succinic acid, maleic acid, fumaric acid, butylene glycol, propylene glycol, and ethylene glycol.
15. The method of claim 12 , wherein said composition comprises 50-95% by weight of said at least one monomer and 5-50% by weight of said reactive diluent.
16. A polymer obtained by the method of claim 8 .
17. The method of making a polymer as claimed in claim 1 , wherein the at least one polymerizable monomer is selected from the group consisting of:
18. The method of making a polymer as claimed in claim 1 , wherein the at least one polymerizable monomer is selected from the group consisting of:
19. The method of making a polymer as claimed in claim 8 , wherein the at least one anhydrosugar-based polymerizable monomer is selected from the group consisting of:
20. The method of making a polymer as claimed in claim 1 , wherein the at least one anhydrosugar-based polymerizable monomer is selected from the group consisting of: